Unprecedented Cyclization Catalyzed by a Cytochrome P450 in Benzastatin Biosynthesis
Benzastatins have unique structures probably derived from geranylated p-aminobenzoic acids. The indoline and tetrahydroquinoline scaffolds are presumably formed by cyclization of the geranyl moiety, but the cyclization mechanism was unknown. We studied the benzastatin biosynthetic gene cluster of St...
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| Published in | Journal of the American Chemical Society Vol. 140; no. 21; pp. 6631 - 6639 |
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| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
30.05.2018
Amer Chemical Soc |
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| Abstract | Benzastatins have unique structures probably derived from geranylated p-aminobenzoic acids. The indoline and tetrahydroquinoline scaffolds are presumably formed by cyclization of the geranyl moiety, but the cyclization mechanism was unknown. We studied the benzastatin biosynthetic gene cluster of Streptomyces sp. RI18; functions of the six enzymes encoded by it were analyzed by gene disruption in a heterologous host and in vitro enzyme assays. We propose the biosynthetic pathway for benzastatins in which a cytochrome P450 (BezE) is responsible for the cyclization of geranylated p-acetoxyaminobenzoic acids; BezE catalyzes elimination of acetic acid to form an iron nitrenoid, nitrene transfer to form an aziridine ring, and nucleophilic addition of hydroxide ion to C-10 and chloride ion to C-9 to generate the indoline and tetrahydroquinoline scaffolds, respectively. Discovery of this enzyme, which should be termed cytochrome P450 nitrene transferase, provides an important insight into the functional diversity of cytochrome P450. |
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| AbstractList | Benzastatins have unique structures probably derived from geranylated p-aminobenzoic acids. The indoline and tetrahydroquinoline scaffolds are presumably formed by cyclization of the geranyl moiety, but the cyclization mechanism was unknown. We studied the benzastatin biosynthetic gene cluster of Streptomyces sp. RI18; functions of the six enzymes encoded by it were analyzed by gene disruption in a heterologous host and in vitro enzyme assays. We propose the biosynthetic pathway for benzastatins in which a cytochrome P450 (BezE) is responsible for the cyclization of geranylated p-acetoxyaminobenzoic acids; BezE catalyzes elimination of acetic acid to form an iron nitrenoid, nitrene transfer to form an aziridine ring, and nucleophilic addition of hydroxide ion to C-10 and chloride ion to C-9 to generate the indoline and tetrahydroquinoline scaffolds, respectively. Discovery of this enzyme, which should be termed cytochrome P450 nitrene transferase, provides an important insight into the functional diversity of cytochrome P450. Benzastatins have unique structures probably derived from geranylated p-aminobenzoic acids. The indoline and tetrahydroquinoline scaffolds are presumably formed by cyclization of the geranyl moiety, but the cyclization mechanism was unknown. We studied the benzastatin biosynthetic gene cluster of Streptomyces sp. RI18; functions of the six enzymes encoded by it were analyzed by gene disruption in a heterologous host and in vitro enzyme assays. We propose the biosynthetic pathway for benzastatins in which a cytochrome P450 (BezE) is responsible for the cyclization of geranylated p-acetoxyaminobenzoic acids; BezE catalyzes elimination of acetic acid to form an iron nitrenoid, nitrene transfer to form an aziridine ring, and nucleophilic addition of hydroxide ion to C-10 and chloride ion to C-9 to generate the indoline and tetrahydroquinoline scaffolds, respectively. Discovery of this enzyme, which should be termed cytochrome P450 nitrene transferase, provides an important insight into the functional diversity of cytochrome P450.Benzastatins have unique structures probably derived from geranylated p-aminobenzoic acids. The indoline and tetrahydroquinoline scaffolds are presumably formed by cyclization of the geranyl moiety, but the cyclization mechanism was unknown. We studied the benzastatin biosynthetic gene cluster of Streptomyces sp. RI18; functions of the six enzymes encoded by it were analyzed by gene disruption in a heterologous host and in vitro enzyme assays. We propose the biosynthetic pathway for benzastatins in which a cytochrome P450 (BezE) is responsible for the cyclization of geranylated p-acetoxyaminobenzoic acids; BezE catalyzes elimination of acetic acid to form an iron nitrenoid, nitrene transfer to form an aziridine ring, and nucleophilic addition of hydroxide ion to C-10 and chloride ion to C-9 to generate the indoline and tetrahydroquinoline scaffolds, respectively. Discovery of this enzyme, which should be termed cytochrome P450 nitrene transferase, provides an important insight into the functional diversity of cytochrome P450. |
| Author | Takagi, Motoki Katsuyama, Yohei Ohnishi, Yasuo Fujie, Manabu Satoh, Noriyuki Shin-ya, Kazuo Izumikawa, Miho Tsutsumi, Hayama |
| AuthorAffiliation | Department of Biotechnology, Graduate School of Agricultural and Life Sciences Collaborative Research Institute for Innovative Microbiology National Institute of Advanced Industrial Science and Technology (AIST) The University of Tokyo |
| AuthorAffiliation_xml | – name: National Institute of Advanced Industrial Science and Technology (AIST) – name: The University of Tokyo – name: Department of Biotechnology, Graduate School of Agricultural and Life Sciences – name: Collaborative Research Institute for Innovative Microbiology |
| Author_xml | – sequence: 1 givenname: Hayama surname: Tsutsumi fullname: Tsutsumi, Hayama organization: The University of Tokyo – sequence: 2 givenname: Yohei surname: Katsuyama fullname: Katsuyama, Yohei email: ayasuo@mail.ecc.u-tokyo.ac.jp organization: Collaborative Research Institute for Innovative Microbiology – sequence: 3 givenname: Miho surname: Izumikawa fullname: Izumikawa, Miho – sequence: 4 givenname: Motoki surname: Takagi fullname: Takagi, Motoki – sequence: 5 givenname: Manabu surname: Fujie fullname: Fujie, Manabu – sequence: 6 givenname: Noriyuki surname: Satoh fullname: Satoh, Noriyuki – sequence: 7 givenname: Kazuo surname: Shin-ya fullname: Shin-ya, Kazuo organization: National Institute of Advanced Industrial Science and Technology (AIST) – sequence: 8 givenname: Yasuo orcidid: 0000-0001-7633-9236 surname: Ohnishi fullname: Ohnishi, Yasuo email: aykatsu@mail.ecc.u-tokyo.ac.jp organization: Collaborative Research Institute for Innovative Microbiology |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/29716187$$D View this record in MEDLINE/PubMed |
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| Keywords | N-OXYGENASE AURF STREPTOMYCES-COELICOLOR A3 CRYSTAL-STRUCTURE NATURAL-PRODUCTS ENZYMES P450 NITROSPOREUS FREE-RADICAL SCAVENGERS FLAVIOLIN SUBSTRATE MOLECULES CELL PROTECTING ACTIVITY |
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Chem. Soc, Perkin Trans.I |
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| Snippet | Benzastatins have unique structures probably derived from geranylated p-aminobenzoic acids. The indoline and tetrahydroquinoline scaffolds are presumably... |
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| SubjectTerms | acetic acid biochemical pathways biosynthesis catalytic activity Chemistry Chemistry, Multidisciplinary chlorides cytochrome P-450 ethyleneimine functional diversity gene targeting genetically modified organisms iron Lewis bases moieties multigene family Physical Sciences Science & Technology Streptomyces transferases |
| Title | Unprecedented Cyclization Catalyzed by a Cytochrome P450 in Benzastatin Biosynthesis |
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